108-28-1Relevant academic research and scientific papers
Deoxyribonolactone formation in photoirradiation of 5-bromouracil-containing oligonucleotides by direct C1′ hydrogen abstraction
Fujimoto, Kenzo,Ikeda, Yutaka,Ishihara, Shigenori,Saito, Isao
, p. 2243 - 2245 (2002)
Mechanistic studies on the formation of deoxyribonolactone by UV irradiation of hexamer d(GC1BrUGC)2 (ODN 2a) containing 1′-deuterio-2′-deoxyadenosine 1 was examined. The kinetic isotope effect (kH/kD) for the f
A Novel Synthesis of Protoanemonin by the Catalytic Vapour-phase Oxidation of Silvan
Iovel, Irina,Goldberg, Yuri,Shymanska, Mariya
, p. 1079 - 1080 (1990)
The vapour-phase oxidation of 2-methylfuran (silvan) in air over vanadium-molybdenum oxide catalysts under specific conditions was unexpectedly found to afford 5-methylenefuran-2(5H)-one (protoanemonin) which is otherwise difficult to obtain.
HETEROORGANIC FURAN DERIVATIVES. 61. TRIMETHYL(5-METHYL-2-FURYL)SILANE AND TRIMETHYL(5-METHYL-2-FURYL)GERMANE
Lukevits, E.,Ignatovich, L. M.,Iovel', I. G.,Gol'dberg, Yu. Sh.,Shimanskaya, M. V.
, p. 15 - 17 (1987)
The transformations of trimethyl(5-methyl-2-furyl)silane and trimethyl(5-methyl-2-furyl)germane were studied upon vapor-phase oxidation by atmospheric oxygen on a V-Mo-Ag-O catalyst.Under these conditions, trimethyl(5-formyl-2-furyl)silane and trimethyl(5-formyl-2-furyl)germane are formed albeit in only 5-7percent yield.This low yield is a consequence of the thermal instability of the starting compounds and the aldehydes formed.The oxidation of 2-methyl-5-tert-butylfuran was studied under comparable conditions.The corresponding aldehyde was obtained in 30percent yield.A scheme was proposed for the catalytic oxidation of 5-substituted 2-methylfurans.
A Convenient Synthesis of Protoanemonin
Crey, Caroline,Dumy, Pascal,Lhomme, Jean,Kotera, Mitsuharu
, p. 3727 - 3732 (2003)
A new convenient synthesis of protoanemonin (1) starting from 2-deoxy-D-ribose (3) is described. A key step in the sequence is the successive β- and δ-eliminations of 3,5-di-O-p-toluoyl-2-deoxy-D-ribono-1,4-lactone (6).
A palladium catalyzed efficient synthesis of γ-methylene-α, β-unsaturated γ-lactones via cyclization of 3,4-alkadienoic acids
Ma, Shengming,Yu, Fei
, p. 9896 - 9901 (2005)
An efficient method was developed for the synthesis of γ-methylene- α,β-unsaturated γ-lactones from the Pd-catalyzed cyclization of 3,4-alkadienoic acids. Control experiment shows that the reaction should be carried out under a N2 atmosphere to ensure the high purity of the products.
A Facile Synthesis of γ-Alkylidene-α,β-unsaturated γ-Lactones
Tsuboi, Sadao,Wada, Hiroshi,Mimura, Shigetoshi,Takeda, Akira
, p. 937 - 938 (1987)
Treatment of β-allenic acid with KI3 gave directly γ-alkylidene-α,β-unsaturated γ-lactones in moderate yields.
Pd/C-Cu mediated direct and one-pot synthesis of γ-ylidene butenolides
Rambabu,Bhavani,Nalivela, Kumara Swamy,Mukherjee, Soumita,Rao, M.V. Basaveswara,Pal, Manojit
, p. 2151 - 2155 (2013)
10% Pd/C in combination with CuI, PPh3, and Et3N has been identified as an effective catalyst system for the coupling of (Z)-3-iodoacrylic acid with terminal alkynes in 1,4-dioxane leading to the one-pot synthesis of γ-ylidene butenolides. The methodology showed remarkable regio- and stereoselectivity as only the five-membered lactone ring products were formed with an exocyclic double bond possessing Z-geometry.
Acid-mediated coupling of γ-hydroxybutenolides and aldehydes: Synthesis of a new class of spirocyclic ketal-lactones
Munoz, Alberto,Murelli, Ryan P.
, p. 6779 - 6781,3 (2012)
In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf), γ-methyl-γ-hydroxybutenolide reacts with aromatic aldehydes to generate a new class of stereochemically rich spirocyclic ketal-lactones in good yields and with excellent stereoselectivities. We believe that this process takes place through the in situ generation of protoanemonin followed by a Prins reaction. Herein, we describe this discovery, along with substrate scope and preliminary mechanistic studies.
Intramolecular Photocycloaddition of 2(5 H)-Furanones to Temporarily Tethered Terminal Alkenes as a Stereoselective Source of Enantiomerically Pure Polyfunctionalyzed Cyclobutanes
Xin, Yangchun,Rodríguez-Santiago, Luís,Sodupe, Mariona,álvarez-Larena, Angel,Busqué, Félix,Alibés, Ramon
, p. 3188 - 3199 (2018)
Allyloxymethyloxymethyl and 4-pentenoyloxymethyl substituents have been used as tethering groups to study the intramolecular [2 + 2] photocycloaddition of chiral 5-substituted 2(5H)-furanones. The photoreactions proceed in good yield and provide the expected regio- and diastereoselective tricyclic compounds with complementary regioselectivity, which depends on whether the vinyl chain is attached to the furanone by an acetal or an ester linkage. Computational simulations agree with experimental observations and indicate that the origin of the different observed regioselectivity in the intramolecular photochemical reaction of lactones 5 and 6 arises from the relative stability of the initial conformers. The synthetic potential of the enantiomerically pure photoadducts is illustrated by preparing an all-cis 1,2,3-trisubstituted cyclobutane bearing fully orthogonally protected hydroxyl groups.
Chemistry of the 2-deoxyribonolactone lesion in oligonucleotides: Cleavage kinetics and products analysis
Roupioz, Yoann,Lhomme, Jean,Kotera, Mitsuharu
, p. 9129 - 9135 (2002)
Deoxyribonolactone in DNA is an oxidized abasic site damage that is produced by a variety of physical and chemical agents such as γ-irradiation and ene-diyne antibiotics. The extent and biological significance of the lesion are poorly documented due to the high lability of the damaged DNA. The chemistry of degradation of deoxyribonolactone-containing DNA was investigated using oligonucleotides of different length (5-, 11-, 23-, 34-mers) in which the lactone was photochemically generated, as already reported, from oligonucleotide precursors containing a photoactive nitroindole residue. The procedure was successfully extended to double-strand synthesis by irradiation of the preformed duplex in which one strand contained the nitroindole residue. The degradation kinetics were investigated as a function of pH, temperature, length, and ionic strength. The cleavage fragments resulting from β- and δ-eliminations were isolated and identified by 1H NMR. It was found that the lesion is extremely sensitive to pH and temperature while slightly dependent upon ionic strength, length, and sequence. The cleavage rates for the β- and δ-elimination steps are of the same order of magnitude. The deoxyribonolactone site leads to greater instability of DNA than the regular deoxyribose abasic site.
